PornPorn Transgender • US
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Train Pickup Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    outdoor pickup
    31:24
    outdoor pickup
    1.1M views
    TRANSFIXED - Femdoms Siri Dahl & Codi Vore Pickup Petite Zariah Aura From The Street To Sex Dungeon
    15:19
    TRANSFIXED - Femdoms Siri Dahl & Codi Vore Pickup Petite Zariah Aura From The Street To Sex Dungeon
    Transfixed
    175.2K views
    outdoor shemale pickup
    31:25
    outdoor shemale pickup
    673.2K views
    Parking Lot Pickup
    08:12
    Parking Lot Pickup
    Kaitlyn Gender
    59.3K views
    Ladyboystar - Bear - I Pickup a 18yo Slender Teen Ladyboy at the Mall
    11:12
    Ladyboystar - Bear - I Pickup a 18yo Slender Teen Ladyboy at the Mall
    Ladyboy Star
    176.6K views
    Ladyboystar - Belle - I Pickup a Super Skinny and Feminine 19yo Ladyboy
    08:12
    Ladyboystar - Belle - I Pickup a Super Skinny and Feminine 19yo Ladyboy
    Ladyboy Star
    177.9K views
    FTM Squirting in Pickup Truck
    02:38
    FTM Squirting in Pickup Truck
    Trip Richards
    61.7K views
    Ladyboystar - Jazz - POV of My Pickup of a Skinny Ladyboy in a Short Dress
    08:12
    Ladyboystar - Jazz - POV of My Pickup of a Skinny Ladyboy in a Short Dress
    Ladyboy Star
    44.3K views
    German Milf Dirty Tina Fuck by Huge Cock bbc and Deepthroat Guy exploited old pickup scheme to penetrate Russian girl
    04:17
    German Milf Dirty Tina Fuck by Huge Cock bbc and Deepthroat Guy exploited old pickup scheme to penetrate Russian girl
    D Dasi_vilage_boy
    7.1K views
    Blond milf with big tits likes double penetration with strangers outdoor in pickup car
    20:00
    Blond milf with big tits likes double penetration with strangers outdoor in pickup car
    Eroticonly
    34.2K views
    curb side pickup
    03:30
    curb side pickup
    16.9K views
    Olivia Love - Pickup Fuck 1
    27:25
    Olivia Love - Pickup Fuck 1
    72.9K views
    Black Tranny Pickup
    04:21
    Black Tranny Pickup
    44.8K views
    Lucky Ramon pickup and fucks hot tranny
    01:14
    Lucky Ramon pickup and fucks hot tranny
    Trans 500
    238.5K views
    stranger pickup slutty crossdresser
    00:20
    stranger pickup slutty crossdresser
    SluttyKittyCD
    9.5K views
    Swallow My Cum
    15:15
    Swallow My Cum
    TSRyley
    247.7K views
    Bimbo Takes on BBC
    08:34
    Bimbo Takes on BBC
    TSRyley
    125.1K views
    How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    106.2K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    742.2K views
    Amateur Couple and Trans - Train
    22:45
    Amateur Couple and Trans - Train
    MySchoolLife
    1M views
    Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    861.5K views
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    15:07
    2 Mommies Training Their TS Slut - Lucy Hart - Penny Barber - Mira Maven
    Lucy Hart
    375.6K views
    POV Hard Pegging Jasmine Dlight From Mistress
    02:17
    POV Hard Pegging Jasmine Dlight From Mistress
    Jasmine_dlight
    125.8K views
    Imagine You Are Fucking a Boy!
    06:15
    Imagine You Are Fucking a Boy!
    KinkyHome
    69.2K views
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    18:27
    Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore
    Vane03_siss
    212.1K views
    2032 - the Bwno Future
    15:06
    2032 - the Bwno Future
    ChristineWest120
    109.8K views
    Trans Girl Bimbo Slut Riding 10-inch BBC while on a Phone Call
    15:58
    Trans Girl Bimbo Slut Riding 10-inch BBC while on a Phone Call
    CaliFauna
    1.8M views
    Gloryhole Cum Slut - Training (unknown PMV artist)
    08:11
    Gloryhole Cum Slut - Training (unknown PMV artist)
    684.7K views
    Playtime 69
    27:02
    Playtime 69
    TSRyley
    69K views
    Between the Lines & Between My Legs
    14:17
    Between the Lines & Between My Legs
    Gray Perrier
    88.5K views
    CD TRAP SISSY EDUCATION TRAINING 101
    01:27:33
    CD TRAP SISSY EDUCATION TRAINING 101
    927.7K views
    Making My Cock Explode
    08:09
    Making My Cock Explode
    TSRyley
    51K views
    All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody
    10:52
    All That Throat Training Pays off: Facefucking Gorgeous Transwife Melody
    Melodyfluffington
    281.5K views
    How to train your sissy ass
    17:41
    How to train your sissy ass
    654.6K views
    Corporate Training - Episode 2
    21:30
    Corporate Training - Episode 2
    TiffanyWarmer
    878.6K views
    You're Straight Right- - Sissy Hypno Training
    03:07
    You're Straight Right- - Sissy Hypno Training
    921.2K views
    A White Boys Purpose
    23:50
    A White Boys Purpose
    Kimberhaven
    600.8K views
    Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    653.9K views
    Fuck Us Both Billy
    08:12
    Fuck Us Both Billy
    TSRyley
    89.8K views
    Mrs Lovings Sissy Training
    10:13
    Mrs Lovings Sissy Training
    2.3M views
    I fuck my stepmom's friend when she's at her house
    07:02
    I fuck my stepmom's friend when she's at her house
    yesid
    460.4K views
    Sissy: A slut documentary
    08:12
    Sissy: A slut documentary
    Brat Perversions
    31K views
    She's Going to Get Her Ass Fucked in the Kitchen
    04:57
    She's Going to Get Her Ass Fucked in the Kitchen
    Emmy Angeles
    311.3K views
    Sissy #1: Accepting Your Destiny
    11:37
    Sissy #1: Accepting Your Destiny
    492.7K views
    Ryley Rails Dominates You
    06:51
    Ryley Rails Dominates You
    TSRyley
    48.2K views
    My Neighbor Fisting My Ass
    08:59
    My Neighbor Fisting My Ass
    Emmy Angeles
    138.6K views
    Sissy's asshole is filled up to a meter deep
    17:25
    Sissy's asshole is filled up to a meter deep
    Drift3-4
    704.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    xHamster

    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025

    Help

    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster

    Legal

    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults